Hexahydropyrazolo[1,2-a]pyrazole → 1-[2-[4-(2-Ethoxycarbonylethyl)phenyl]ethyl]-1,5-diazacyclooctane

HRID 55326Notes

Reaction equation

HRID 55326 reaction equation
[CH2:1]([O:3][C:4](/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15]Br)=[CH:10][CH:9]=1)=[O:5])[CH3:2].[N:17]12[CH2:24][CH2:23][CH2:22][N:21]1[CH2:20][CH2:19][CH2:18]2>C(OCC)C>[CH2:1]([O:3][C:4]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][N:17]2[CH2:24][CH2:23][CH2:22][NH:21][CH2:20][CH2:19][CH2:18]2)=[CH:10][CH:9]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 138483Hexahydropyrazolo[1,2-a]pyrazoleHCID 199575382-[4-[(E)-2-ethoxycarbonylvinyl]phenyl]ethyl bromide

Product 1

HCID 199575251-[2-[4-(2-Ethoxycarbonylethyl)phenyl]ethyl]-1,5-diazacyclooctaneYield 104.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-[4-[(E)-2-ethoxycarbonylvinyl]phenyl]ethyl bromide (2.10 g) in diethyl ether (20 ml) was added 1,5-diazabicyclo[3,3,0]octane (0.89 g), and the mixture was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure. To a solution of the residue in ethanol (30 ml) was added a 10% palladium on activated carbon (0.44 g), and the mixture was stirred at room temperature for 5 hours under an atmosphere of hydrogen. The catalyst was removed by filtration through a celite column, and the filtrate was concentrated under reduced pressure. The residue was quenched with an aqueous 1N-NaOH solution (20 ml), and the mixture was extracted with methylene chloride (30 ml). The extract was dried over anhydrous MgSO4, and concentrated to dryness under reduced pressure to give 1-[2-[4-(2-ethoxycarbonylethyl)phenyl]ethyl]-1,5-diazacyclooctane (2.46 g) as a colorless oily liquid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionTo a solution of the residue in ethanol (30 ml) was added a 10% palladium on activated carbon (0.44 g)
  3. stirringthe mixture was stirred at room temperature for 5 hours under an atmosphere of hydrogen
  4. customThe catalyst was removed by filtration through a celite column
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was quenched with an aqueous 1N-NaOH solution (20 ml)
  7. extractionthe mixture was extracted with methylene chloride (30 ml)
  8. dry with materialThe extract was dried over anhydrous MgSO4
  9. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f0b33e3d823345178691c4a8af7dfb9b
Source dataset
uspto-grants-1997_04
Patent number
US05624948

Reaction notes

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